10 Awkward Hollywood Cameos by Tech Founders

If you want to know why technology executives aren’t video stars, look no further than these eight founders – plus one founder’s dog – trying to look natural in movies, TV shows, and commercials. Their performances are glitchier than Facebook’s privacy page.

It’s easy for Silicon Valley’s top nerds to feel like gods among men as they long as they remain within the high-tech bubble, where big codebases and escalating revenues are more important than good looks or interpersonal finesse. And some, like Facebook’s Mark Zuckerberg, can cross over into mainstream celebrity when there’s a real star to do the heavy lifting, like Zuck’s Social Network doppelganger Jesse Eisenberg.

But stick a tech bigwig in front of an actual camera and their inclination to commune, Borg-like, with computing machines becomes a liability. For evidence, look no further than the gallery above.

Tech founders' stiffness as entertainers is unfortunate; as analog art converges with digital networks, a great many Silicon Valley companies – Apple, Google, Netflix, Pandora, etc. – need to get cozier with Hollywood. Maybe shareholders should start looking for more natural ambassadors. If Ashton Kutcher and Justin Bieber ever get tired of their showbiz careers, they may be able to find new gigs in tech. At the top.

Above: Dennis Crowley, Family Feud

He might have looked goofy on Family Feud, but Foursquare founder Dennis Crowley considers his 2009 appearance on the game show to be a greater accomplishment than selling his first startup to Google. "My brother’s been wanting to do this for 20 years," Crowley told branding guru Dan Schawbel. His brood emerged victorious, as did Crowley: The CEO brags on his homepage about winning the Feud's "Fast Money" round. Survey says, not bad. Not bad at all.

Mark Cuban, Dancing With the Stars

Neither six hours a day of practice nor prior cameos on Walker, Texas Ranger prepared Cuban to please the Dancing With the Stars cameras. Cuban and his partner were eliminated in the fifth round of judging, an inglorious fall from the glory days of the late 1990s, when Cuban sold Broadcast.com to Yahoo for $5.9 billion (about one-third of what all of Yahoo is worth today).

Scott McNealy's dog, Dumbarton Bridge

Scott McNealy's pet pooch "Network" ended up in this independent film after McNealy's Sun Microsystems put $150,000 into the movie. Sadly, the film, about a Vietnam vet and his high-tech girlfriend, proved to be a bit of a dog. Sun's then-HQ (now occupied by Facebook) anchored one end of the real Dumbarton Bridge, which happens also to be the ugliest bridge that crosses the San Francisco Bay.

Larry Ellison, Iron Man 2

After being pegged as the off-screen inspiration for Robert Downey Jr.'s rendering of Tony Stark in the first Iron Man movie, Oracle founder Larry Ellison was brought into the superhero movie's sequel live and in the flesh. Ellison greets Downey Jr.'s character on a stairway as "the Oracle" and calls out, "call me" -- which is about as obsequious as you could ever hope to see Ellison.

Shawn Fanning, The Italian Job

This heist remake earned only middling scores from reviewers, but Napster co-founder Fanning was sensible enough to play himself. He also managed to steer clear of driving a Mini like everyone else in the movie.

Elon Musk, Iron Man 2

For such an admirably bold entrepreneur – he invests in space rockets, electric cars, and solar panels, with a surprising degree of success – Tesla CEO Elon Musk sure swallows his line when he offers Downey a briefing on an "electric jet."

Biz Stone, Stoli Gala Applik

Twitter may be a "triumph of the human spirit," as co-founder Biz Stone once wrote, but apple-flavored vodka is more of a villain in the world of hard-core mixology, fueling such sickly-sweet concoctions as the candy-apple martini. Maybe that's why Stone, chatting with a mirror image of himself in an ad for Stoli Gala Applik, doesn't even try to convince himself to drink the stuff, spending virtually the entire ad talking about his microblogging startup. Na zdorovie!

Steve Wozniak, Dancing With the Stars

Apple co-founder Steve Wozniak is one of the nicest guys in tech, so it pains us to point out that he finished dead last in his first two performances on Dancing With the Stars. It pained Wozniak, too; at one point he suspected the voting might be rigged against him. We think maybe his feet were to blame.

Mark Zuckerberg, The Simpsons

Facebook CEO Mark Zuckerberg's first line in his Simpsons cameo made fun of his own awkwardness, while the second made fun of the fact that he dropped out of college. It's hard to throw rocks at someone who has already criticized himself. Nicely played, Zuck.

Bill Gates, Frasier

Microsoft co-founder Bill Gates shows up as himself in the 200th
episode of NBC's Frasier, playing a guest on the Seattle radio show
run by the sitcom's namesake character Frasier Crane. Crane flies into
a jealous rage as Gates usurps him, answering computer questions from
callers who normally seek the host's psychiatric expertise.

The bit allowed Gates, then Microsoft's chairman, to tout features of the
company's Windows XP operating system -- back before XP became
infamous for its vulnerability to spyware and other internet viruses.